Landing Love

Jill Hinckley looks out over Portland Harbor. She and her family have enjoyed navigating the Maine waters for generations.

Originally from Southwest Harbor, Hinckley now lives on Munjoy Hill.

Jill Hinckley, left, and her assistant Carolyn Clement, at the Portland office of Hinckley Introductions.

On February 1, 2018

By: Dr. Lisa Belisle Photography: Nicole Wolf

Jill Hinckley brings skills honed in the boat business to relationship navigation.

Jill Hinckley enjoys helping her matchmaking clients chart a course through unfamiliar waters. For adults over 40, whether divorced, widowed, or never married, trying to find connection in the strange new world of digital dating can be daunting. With her cheerful smile and professional demeanor, 54-year-old Hinckley puts people at ease. As the owner of Hinckley Introductions, she uses her well-honed intuition—and extensive database—to get people off their islands of loneliness and point them toward the (not-so-distant) shores of love.

The boating metaphors are apt because the Hinckley family has a longstanding affinity for the ocean. Jill’s grandfather, Henry R. Hinckley, founded Hinckley Yachts at a small boatyard in Southwest Harbor in 1928. “When my grandfather owned the Hinckley company, we only built 12 boats a year,” says Jill, who was born in Ellsworth and grew up in Southwest Harbor. “It took at least a year to build a boat. Each family was very important. We knew every boat name, every customer.” Hinckley herself worked in multiple capacities for the business, from giving tours of the boatyard as a high-school student, to working on the dock during college, and participating in retail operations as an adult. “I grew up with very personal relationships,” says Hinckley. “I loved networking and getting to know people.”

After her father sold the business in 1998, Hinckley worked in the marine recruiting industry, which allowed her to capitalize on her prior experience. “You’re connecting businesses with employees,” says Hinckley, who by that time had remarried and moved away from Southwest Harbor. “You’re interviewing people and understanding what they want, where they’re going, where they want to live.”

Four years ago, Hinckley launched a new relationship-based venture: Hinckley Introductions. Perhaps without realizing it, Hinckley had become involved in combatting a growing public health problem: loneliness. According to studies done by Dr. Julianne Holt- Lunstad and her colleagues at Brigham Young University in Provo, Utah, the risk of premature death is 50-percent lower for adults who have a greater connection with others, compared with those who are socially isolated. Loneliness is worse for one’s health than being obese or smoking 15 cigarettes a day, the studies found.

“There are a lot of different ways you can step into the dating world,” says Hinckley. She tailors her services according to her clients’ needs, from being part of her database (a free service) to coaching and personal matchmaking. “We try to take baby steps,” says Hinckley. “We don’t want to throw people into this without all the tools they need to get through this experience.” Hinckley begins by having potential clients fill out an extensive questionnaire, which explores everything from interests and occupation to political and religious views. “There are some deal-breakers,” says Hinckley. “In this crazy world we live in today, politics can be a big one.” For those who want coaching, Hinckley offers advice on topics such as online dating applications. The mother of five children, ages 15 to 30, Hinckley often relies on her older kids for the latest technology information. “I need them to teach me how to use these apps,” she says, mentioning Bumble, a newer app that places a high premium on safety. “Then I pass that information on to my clients,” says Hinckley. “They’re a big help to me.”

Hinckley works with 10 to 15 personal matchmaking clients each year. “Timing is really important for matchmaking because we jump right into it,” says Hinckley. “We get excited about meeting you and deciding who we are going to set you up with, so you have to be ready. You have to fit this into your life.” Hinckley and her assistant, Carolyn Clement, try to determine the most optimal matches, sorting through the information they have gathered, doing background checks, and setting up the initial contact for a potential couple.

Hinckley has found a niche with clients who share a love of boats and the ocean. Although many of them are from Maine, a high percentage of them also travel to other parts of the country, especially in the winter. Hinckley collaborates with others in her field, some as far away as Europe, to find good candidates for her clients. “I love working with other matchmakers,” says Hinckley. “If another matchmaker in Boston, for example, has a client they’re working with, they might contact me and see if anybody in my database or anybody I’m working with might match up with their client.”

The matchmaking business is growing in popularity. Some matchmakers work with a large staff, spread over multiple offices in larger states like New York and California. Hinckley, who recently opened a second office in Boston, is always seeking to further her knowledge in the field. She belongs to the New York-based Matchmaking Institute and attends its yearly conference. “We take this very seriously,” says Hinckley.

Hinckley says that some of the best matches are between those who may seem to have little in common at first. “I’m generally not as outgoing as my husband is, for example,” says Hinckley, who has been married to Sandy Spaulding for 18 years. “We complement each other so well, and we laugh, we have fun. We have differences that we celebrate.” Hinckley and her husband agree on core values, like the importance of family. They also share a fondness for the deep blue sea. “We do love to go boating and that was really important to me,” she says.

Hinckley has remained true to her family legacy, not simply as an ocean enthusiast, but also as one who believes in the power of human interaction. “Recruiting and the boat business brought me to matchmaking,” says Hinckley. “I like to connect people in a personal and meaningful way. This is how I do it.”